An efficient and general entry to (Z)-α-fluoro-β-substituted acrylaldehydes based on the coupling reaction of α-fluoro-β-amino acrylaldehydes with organolithium reagents

Article abstract of DOI:10.1246/cl.1997.739

α-Fluoro-β-amino acrylaldehydes (2), readily available from the reaction of polyfluoroalkenyl tosylates (1) with dialkylamines in the presence of triethylamine and a catalytic amount (10 mol%) of tetrabutylammonium fluoride (TBAF), reacted smoothly with various organolithium reagents at -78 °C for 0.5 h, followed by hydrolysis with 10% hydrochloric acid at room temperture for 1 h to afford the corresponding (Z)-α-fluoro-β-substituted acrylaldehydes (3) via allylic rearrangement in good to excellent yields.